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How Carly Fiorina Confounded Donald Trump

Fiorina, the former CEO of Hewlett-Packard, was ready to exploit a vulnerability that Trump revealed on Wednesday night: He doesn't really know how to respond when women challenge him.

Posted on September 17, 2015, at 3:25 a.m. ET

Mark J. Terrill / AP Images

SIMI VALLEY, California —  She savaged his business record. She dismissed him as an entertainer. She undermined him with the most withering one-liner of the night.

But perhaps the most notable achievement in Carly Fiorina's dispatching of Donald Trump during Wednesday's Republican presidential debate was that her barbs often seemed to leave the loudmouth billionaire speechless — and seething.

For a candidate known to ridicule his rivals with reckless abandon, Trump struggled all night to respond to Fiorina's criticism — sometimes countering with cringe-inducing condescension, other times shriveling into an uncharacteristically quiet display of head-shaking and tongue-biting. He appeared to reveal a weakness that could be especially damaging to any Republican presidential nominee next year: Trump doesn't know what to do when women challenge him.

And Fiorina, the former CEO of Hewlett-Packard, who prides herself on a career of busting up boys clubs, came prepared to exploit Trump's vulnerability.

The onstage showdown between the two candidates was highly anticipated in the days leading up to the debate, after Rolling Stone published an article that quoted Trump ridiculing Fiorina's appearance.

"Look at that face!" the billionaire reportedly joked while watching her on TV. "Would anyone vote for that? Can you imagine that, the face of our next president?! ... I mean, she's a woman, and I'm not s'posedta say bad things, but really, folks, come on. Are we serious?"

Amid the ensuing outrage, Trump claimed — in a rare walk-back — that he was referring to Fiorina's "persona," not her looks. When she was asked to respond at Wednesday's debate, the candidate said simply, "I think women all over this country heard very clearly what Mr. Trump said." The audience greeted the line with loud and sustained applause, while Trump stood largely motionless waiting for it to subside.

Finally, he leaned into the microphone and delivered a retort that seemed intended as friendly and playful. "I think she's got a beautiful face," he pronounced, "and I think she's a beautiful woman." The crowd in the debate hall fell awkwardly silent, while audible groans rippled across the room where reporters were covering the debate.

At other moments on Wednesday night, Trump resisted the temptation to take Fiorina's bait, by redirecting his hostility toward others on the stage. When, for example, she dismissively referred to Trump as "entertaining" and questioned his seriousness, he responded by arbitrarily picking on Rand Paul — and effectively letting her attack stand.

Asked about Fiorina's pre-debate preparations for Trump, deputy campaign manager Sarah Isgur Flores told BuzzFeed News, "It's really just Carly being Carly. ... She's fearless. This is all her. Carly won't be intimidated."

Fiorina has spoken in the past about confronting sexism in the corporate world. In her memoir, Tough Choices, she wrote:

From the first stories of my hiring until the last of my firing, both the language and the intensity of the coverage were different for me than for any other CEO. It was more personal, with much commentary about my personality and my physical appearance, my dress, my hair or my shoes. That first week, the editor of BusinessWeek came to see me with the beat reporter because they'd been working on a story for several months. Hewlett-Packard was going to be the cover story whether we liked it or not, and everyone recommended that I talk with them. Before we'd even sat down, the very first question from the editor was "Is that an Armani suit you're wearing?"

Vanity Fair, despite being warned numerous times that they were writing fiction about me, continued to report that I traveled constantly with a hairdresser and a makeup artist. There was a persistent rumor, bolstered by commentary in the local press, that I'd built a pink marble bathroom in my office...

I was alternatively described as "flashy" or "glamorous" or "diamond studded," which frequently was translated to mean a superficial "marketing" type.

Trump, meanwhile, has already struggled this campaign cycle with being challenged by a woman. After Fox News host Megyn Kelly aggressively grilled him at last month's Republican debate, he launched a high-profile, days-long feud that ultimately culminated in his suggesting that Kelly had been menstruating during the event.

He also has a well-documented penchant for defining and categorizing women according to their attractiveness, as noted recently in the Washington Post. In a 2006 book, for example, Trump compared women to pricey objects: "Beauty and elegance, whether in a woman, a building, or a work of art is not just superficial or something pretty to see."

In 2012, he tweeted that Arianna Huffington was "unattractive both inside and out," and added, "I fully understand why her former husband left her for a man — he made a good decision." And once, when New York Times columnist Gail Collins wrote something about him that he didn't like, he reportedly sent her a copy of the article with the words, "The face of a dog!" scrawled over her photo.

In the spin room after the debate Wednesday, Russ Schriefer, a senior adviser to Chris Christie, stressed that it was crucial for Republicans to nominate someone capable of debating Hillary Clinton without alienating women voters.

"Whoever wins the Republican nomination will have to do much better with women than in 2012," said Schriefer, noting that Christie — a candidate known, like Trump, for his aggressive political style — managed to win re-election against Barbara Buono in 2013 with a majority of women voters in New Jersey.

Christie didn't pull his punches during that race, Schriefer said, but nor did he come off as patronizing or sexist. The key: "You have to attack in the right way. ... You can't be condescending. You have to respect your opponent, as your opponent. That's all that women expect."

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